The album arose out of Blueprint of a Lady: The Once and Future Life of Billie Holiday, Freelon's collaboration with choreographer Ronald K. Brown. The two created a multimedia tribute to Holiday—with music, dance, and video—that Neelon and Ronald K. Brown/Evidence premiered at Jacob's Pillow Dance Festival in June.
"I was having dinner with Ron," Freelon said in a statement, "and telling him how much I loved and admired Billie Holiday and talking about my dreams of doing a tribute to her. His concept was more along the lines of expressing through the body the impact she had on all of us. That project became a three-part collaboration of live band, dancers, and video, with each of us expressing our own interpretation of what it means to be an artist, to tell your own story. It was an experimental venture with Billie as touchstone."
Freelon's album comprises 15 tracks, including such Holiday classics as "God Bless the Child," "Don't Explain," and "Strange Fruit," plus one of Freelon's own songs, "Only You Will Know," a duet with guitarist Andr_ Bush that imagines a conversation between Holiday and an ing_nue. The ing_nue, Freelon said, "[asks] her questions like 'what would you do?', 'how can I sound like you?', 'should I wear a flower in my hair?', and Billie answers her the only way a sesasoned person could anser: be yourself. One of those easy to say, hard to do things."